This paper presents the observations and reflections of four faculty members who developed experiential online learning pathways for students in diverse professional programs. In relation to programmatic expectations of Nursing, Education and Business, the challenges and opportunities for experiential online learning design are discussed. In addition, the scaffolding and development of online learning within an undergraduate degree, which ladders into professional programming, are presented. Using Kolb's Experiential Model of learning design to structure the discussion, the faculty members reflect on the success of implementation from their various positions as leaders and instructors of programs. They seek to answer questions for themselves and their faculties in relation to the feasibility of designing experiential learning opportunities online and how this can contribute to deepening professional practice. The paper closes with implications for practice for other post-secondary educators who may be considering experiential online learning.